US4092148A - Amide derivatives of 1,3,4-thiadiazoles - Google Patents
Amide derivatives of 1,3,4-thiadiazoles Download PDFInfo
- Publication number
- US4092148A US4092148A US05/012,135 US1213570A US4092148A US 4092148 A US4092148 A US 4092148A US 1213570 A US1213570 A US 1213570A US 4092148 A US4092148 A US 4092148A
- Authority
- US
- United States
- Prior art keywords
- hydrogen
- trifluoromethyl
- sub
- composition
- chlorodifluoromethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 Amide derivatives of 1,3,4-thiadiazoles Chemical class 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 239000000460 chlorine Substances 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 239000011737 fluorine Substances 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical group 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 14
- 230000002363 herbicidal effect Effects 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 18
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims 8
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 8
- 229930195733 hydrocarbon Natural products 0.000 abstract description 8
- 239000004009 herbicide Substances 0.000 abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 239000000575 pesticide Substances 0.000 abstract description 2
- 150000004867 thiadiazoles Chemical class 0.000 abstract description 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- 239000004480 active ingredient Substances 0.000 description 18
- 238000009472 formulation Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LTEUXHSAYOSFGQ-UHFFFAOYSA-N 5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=C(C(F)(F)F)S1 LTEUXHSAYOSFGQ-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 3
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 2
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- 244000055702 Amaranthus viridis Species 0.000 description 2
- 235000004135 Amaranthus viridis Nutrition 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 235000009344 Chenopodium album Nutrition 0.000 description 2
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 2
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 2
- 240000008067 Cucumis sativus Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 2
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000010440 gypsum Substances 0.000 description 2
- 229910052602 gypsum Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 235000021332 kidney beans Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- VBJIFLOSOQGDRZ-UHFFFAOYSA-N (2-chloro-2,2-difluoroacetyl) 2-chloro-2,2-difluoroacetate Chemical compound FC(F)(Cl)C(=O)OC(=O)C(F)(F)Cl VBJIFLOSOQGDRZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DKYIAODFDHXSHC-UHFFFAOYSA-O 2,2,2-trichloro-N-[5-chloro-1-(difluoromethyl)-1,3,4-thiadiazol-1-ium-2-yl]acetamide Chemical compound O=C(C(Cl)(Cl)Cl)NC([S+]1C(F)F)=NN=C1Cl DKYIAODFDHXSHC-UHFFFAOYSA-O 0.000 description 1
- NUBLZNKMBSBWLO-UHFFFAOYSA-N 2,2,2-trichloro-n-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC(F)(F)C1=NN=C(NC(=O)C(Cl)(Cl)Cl)S1 NUBLZNKMBSBWLO-UHFFFAOYSA-N 0.000 description 1
- CGDPMVVAHJKNIN-UHFFFAOYSA-N 2,2,2-trichloro-n-methyl-n-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound ClC(Cl)(Cl)C(=O)N(C)C1=NN=C(C(F)(F)F)S1 CGDPMVVAHJKNIN-UHFFFAOYSA-N 0.000 description 1
- LVKJUFHONRYUSO-UHFFFAOYSA-N 2,2,2-trifluoro-n-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]acetamide Chemical compound FC(F)(F)C(=O)NC1=NN=C(C(F)(F)F)S1 LVKJUFHONRYUSO-UHFFFAOYSA-N 0.000 description 1
- PSAKKOKLSDIKEK-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetamide Chemical compound NC(=O)C(F)(F)Cl PSAKKOKLSDIKEK-UHFFFAOYSA-N 0.000 description 1
- OAWAZQITIZDJRB-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetic acid Chemical compound OC(=O)C(F)(F)Cl OAWAZQITIZDJRB-UHFFFAOYSA-N 0.000 description 1
- DKICDIOGDYHJLU-UHFFFAOYSA-N 2-methyl-n-[5-(1,1,2,2,2-pentafluoroethyl)-1,3,4-thiadiazol-2-yl]propanamide Chemical compound CC(C)C(=O)NC1=NN=C(C(F)(F)C(F)(F)F)S1 DKICDIOGDYHJLU-UHFFFAOYSA-N 0.000 description 1
- TTWHKDGONBRWOB-UHFFFAOYSA-N 2-methyl-n-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]propanamide Chemical compound CC(C)C(=O)NC1=NN=C(C(F)(F)F)S1 TTWHKDGONBRWOB-UHFFFAOYSA-N 0.000 description 1
- NGOZZJNCZLAIPT-UHFFFAOYSA-N 5-(1,1,2,2,2-pentafluoroethyl)-1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=C(C(F)(F)C(F)(F)F)S1 NGOZZJNCZLAIPT-UHFFFAOYSA-N 0.000 description 1
- DQDXANATYZFHQH-UHFFFAOYSA-N 5-chloro-1-(difluoromethyl)-1,3,4-thiadiazol-1-ium-2-amine Chemical compound NC([S+]1C(F)F)=NN=C1Cl DQDXANATYZFHQH-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000001549 Ipomoea eriocarpa Species 0.000 description 1
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 101150108015 STR6 gene Proteins 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000006838 isophorone group Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- LGUJEEIEWRPRKJ-UHFFFAOYSA-N n-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]cyclopropanecarboxamide Chemical compound S1C(C(F)(F)F)=NN=C1NC(=O)C1CC1 LGUJEEIEWRPRKJ-UHFFFAOYSA-N 0.000 description 1
- ARAFQFMXQDBEPU-UHFFFAOYSA-N n-methyl-5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine Chemical compound CNC1=NN=C(C(F)(F)F)S1 ARAFQFMXQDBEPU-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Definitions
- the present invention relates to thiadiazoles and, more particularly to amide derivatives of 1,3,4-thiadiazoles having a halogenated alkyl group in the 5-position. It is known in the art that various types of thiadiazole compositions may be used for pesticidal purposes. For example, Belgian Pat. No. 721,034 teaches that certain compounds, only generally related to that taught in the present invention, have herbicidal properties. However, the particular compounds of the present invention are believed to have biological activity which has heretobefore not known nor anticipated.
- amide derivatives of 1,3,4-thiadiazoles having the general structure: ##STR2## wherein R 1 is a halogenated C 1 to C 4 acyclic hydrocarbon radical, wherein the halogen is fluorine, chlorine and/or bromine
- R 2 is hydrogen or a C 1 to C 4 acyclic hydrocarbon radical
- R 3 is hydrogen, a C 1 to C 4 acyclic hydrocarbon radical, a halogenated C 1 to C 4 acyclic hydrocarbon radical or cycloalkyl.
- R 1 , R 2 and R 3 will have the same definition throughout the specification and claims.
- the compounds show highly desirable activity as agricultural pesticides, particularly as herbicides, for controlling a broad spectrum of unwanted and undesirable weeds and plants.
- the compounds (I) of the invention may be prepared by methods generally known in the art. For example, the following reactions may be employed:
- R 1 is a halogenated lower alkyl radical containing from 1 to 4 carbon atoms, the halogen being selected from fluorine, chlorine, bromine, preferably fluorine;
- R 2 is a lower alkyl radical containing from 1 to 4 carbon atoms and R 3 is hydrogen, a lower alkyl radical containing 1 to 4 carbon atoms; a halogenated lower alkyl radical, the halogen being fluorine, chlorine or bromine or a cycloalkyl radical having from 1 to 4 carbon atoms.
- a mixture containing 5.07 gms of 2-amino-5-trifluoromethyl-1,3,4-thiadiazole, 9.68 gms of chlorodifluoroacetic anhydride and 5 mls of chlorodifluoroacetic acid were heated at a about 100° C for 1 hour and heated an additional 1 hour at about 120° C.
- the reaction mixture was subsequently poured into benzene, mixed thoroughly and the benzene decanted from the insoluble material.
- the benzene solution was concentrated under vacuum to give a solid which was recrystallized from in a benzene/n-hexane mixture.
- the resulting product was identified to be N-(5-trifluoromethyl-1,3,4-thiadiazole) chlorodifluoroacetamide and having a melting point of 150° - 152° C.
- the resulting solid material was separated by filtering and subsequently recrystallized from benzene to provide a product identified to be N-(5-trifluoromethyl)-1,3,4-thiadiazol-2-yl) dichloroacetamide having a melting point of 173.5° - 174.5° C.
- the compounds of the invention have utility as herbicides. Some of them may be applied to soil for use as pre- and post-emergence herbicides. Others may be used in various states of purity ranging, for example, from purified crystals to a technical crude grade. Suitable solvents for these compounds include alcohols, aqueous alcohol and ketone solutions, including acetone, and related ketones such as methyl isobutyl ketone.
- the test procedure involved preparation of the indicated compounds as 50% wettable powders which were extended in water to obtain final spray suspensions.
- the active ingredient was applied at the rates (i.e. expressed as pounds of active compound per acre) indicated in the Table.
- Tests were made on pigweed, setaria, Johnson Grass, morning glory, tomatoes, oats, wheat, cucumbers, red kidney beans (RKB), and cotton. Generally these plants were two weeks of age at the time of application. In the case of cotton, it was in its four to six leaf stage at the time of spray application.
- the red kidney beans, when sprayed, were at a point in their growth where they had a well expanded set of first true leaves.
- Table 3 shows additional herbicidal activity of the compounds of the invention.
- the first numbers in the ratio indicate the phytotoxicity rating from 0 to 10 as previously described.
- the second number or letter indication is whether or not there was evidence of Necroses (Ne), Retardation of growth (R), or no effect at all (0), e.g. 9:Ne.
- compounds of the invention When utilized for herbicidal purposes, compounds of the invention may be formulated in a variety of ways and concentrations for application to the locus of desired vegetation control. It is recognized that the particular type and concentration of formulation, as well as the mode of application of the active ingredient, may govern its biological activity in a given application.
- Compounds of the invention may be prepared as simple solutions of the active ingredient in an appropriate solvent in which it is completely soluble at the desired concentration.
- solvent systems include water, alcohols, acetone, aqueous alcohol and acetone and other organic solvents.
- These simple solutions may be further modified by the addition of various surfactants, emulsifying or dispersing agents, colorants, odorants, antifoaming agents, other herbicides or herbicidal oils which supplement or synergize the activity of the herbicides of the invention, or other adjuvants for any given application where deemed desirable to impart a particular type or degree of plant responses.
- compositions containing the active ingredient include, for example, compositions containing the active ingredient as granules of relatively large particle size, as powder dusts, as wettable powders, as emulsifiable concentrates or as a constituent part of any other known type of formulation commonly utilized by those skilled in the art.
- Such formulations include the adjuvants and carriers normally employed for facilitating the dispersion of active ingredient for agricultural and industrial applications of phytotoxicants. These formulations may contain as little as 0.25% or more than 95% by weight of the active ingredient.
- Dust formulations are prepared by mixing the active ingredient with finely divided solids which act as dispersants and carriers for the phytotoxicant in applying it to the locus of application for vegetation control.
- Typical solids which may be utilized in preparing dust formulations of the active ingredients of the invention include talc, kieselguhr, finely divided clay, fullers' earth, or other common organic or inorganic solids.
- Solids utilized in preparing dust formulations of the active ingredient normally have a particle size of 50 microns or less. The active ingredient of these dust formulations is present commonly from as little as 0.25% to as much as 30% or more by weight of the composition.
- Granular formulations of the active ingredients are prepared by impregnating or adsorbing the toxicant on or into relatively coarse particles of inert solids such as sand, attapulgite clay, gypsum, corn cobs or other inorganic or organic solids.
- the active ingredient of these granular formulations is commonly present from 1.0% to as much as 20.0% or more by weight of the composition.
- Wettable powder formulations are solid compositions of matter wherein the active ingredient is absorbed or adsorbed in or on a sorptive carrier such as finely divided clay, talc, gypsum, lime, wood flour, fullers' earth, kiesselguhr, or the like. These formulations preferably are made to contain 50% to 80% of active ingredient. These wettable powder formulations commonly contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion in water or other liquid carrier utilized to distribute the phytotoxicant to the locus of desired vegetation control.
- a sorptive carrier such as finely divided clay, talc, gypsum, lime, wood flour, fullers' earth, kiesselguhr, or the like. These formulations preferably are made to contain 50% to 80% of active ingredient.
- These wettable powder formulations commonly contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion in water or other liquid carrier utilized to distribute the phytotoxic
- Emulsifiable concentrate formulations are homogeneous liquid or paste compositions containing the active ingredient which will disperse in water or other liquid carrier to facilitate application of the phytotoxicant to the locus of desired vegetation control.
- Such emulsifiable concentrate formulations of the active ingredients may contain only the active ingredient with a liquid or solid emulsifying agent or may contain other relatively nonvolatile organic solvents such as isophorones, dioxane, heavy aromatic naphthas, xylene, or dimethyl formamide.
- the active ingredient in such formulations commonly comprises 10.0% to 70.0% by weight of the phytotoxicant composition.
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Abstract
Novel thiadiazole compounds are taught and disclosed having the following general structure: ##STR1## wherein R1 is a halogenated C1 to C4 acyclic hydrocarbon radical, wherein the halogen is fluorine, chlorine and/or bromine,
R2 is hydrogen or a C1 to C4 acyclic hydrocarbon radical, and
R3 is hydrogen, a C1 to C4 acyclic hydrocarbon radical, a halogenated C1 to C4 acyclic hydrocarbon radical or cycloalkyl.
The compounds show particular utility as agricultural pesticides and, most favorably, as herbicides.
Description
The present invention relates to thiadiazoles and, more particularly to amide derivatives of 1,3,4-thiadiazoles having a halogenated alkyl group in the 5-position. It is known in the art that various types of thiadiazole compositions may be used for pesticidal purposes. For example, Belgian Pat. No. 721,034 teaches that certain compounds, only generally related to that taught in the present invention, have herbicidal properties. However, the particular compounds of the present invention are believed to have biological activity which has heretobefore not known nor anticipated.
In accordance with the present invention, certain amide derivatives of 1,3,4-thiadiazoles are provided having the general structure: ##STR2## wherein R1 is a halogenated C1 to C4 acyclic hydrocarbon radical, wherein the halogen is fluorine, chlorine and/or bromine
R2 is hydrogen or a C1 to C4 acyclic hydrocarbon radical, and
R3 is hydrogen, a C1 to C4 acyclic hydrocarbon radical, a halogenated C1 to C4 acyclic hydrocarbon radical or cycloalkyl.
The particular designation of R1, R2 and R3 will have the same definition throughout the specification and claims.
The compounds show highly desirable activity as agricultural pesticides, particularly as herbicides, for controlling a broad spectrum of unwanted and undesirable weeds and plants.
The compounds (I) of the invention may be prepared by methods generally known in the art. For example, the following reactions may be employed:
1. The reaction of primary or secondary amines with acid anhydrides, e.g. ##STR3## 2. The reaction of primary or secondary amines with an acid, e.g. ##STR4## 3. The reaction of primary or secondary amines with acyl halides, with or without an acid acceptor such as tertiary amines, pyridine, sodium carbonate, etc., e.g. ##STR5## where X = F, Cl or Br
In the compounds of the present invention, it is preferred that R1 is a halogenated lower alkyl radical containing from 1 to 4 carbon atoms, the halogen being selected from fluorine, chlorine, bromine, preferably fluorine; R2 is a lower alkyl radical containing from 1 to 4 carbon atoms and R3 is hydrogen, a lower alkyl radical containing 1 to 4 carbon atoms; a halogenated lower alkyl radical, the halogen being fluorine, chlorine or bromine or a cycloalkyl radical having from 1 to 4 carbon atoms.
The following examples are illustrative of the invention and are not intended to limit the scope thereof.
Six grams of 2-amino-5-trifluoromethyl-1,3,4-thiadiazole were dissolved in 20 mls of trifluoroacetic anhydride and refluxed for about 2 hours and subsequently concentrated under vacuum. The residue weighing 9.1 gms was recrystallized from ethyl acetate/n-hexane to provide a product identified to be N-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl) trifluoroacetamide having a melting point of 168° - 170° C.
______________________________________ C H N ______________________________________ C.sub.5 HF.sub.6 N.sub.3 OS Required, % 22.66 0.38 15.86 Found, % 22.75 0.42 15.74 ______________________________________
A mixture containing 5.07 gms of 2-amino-5-trifluoromethyl-1,3,4-thiadiazole, 9.68 gms of chlorodifluoroacetic anhydride and 5 mls of chlorodifluoroacetic acid were heated at a about 100° C for 1 hour and heated an additional 1 hour at about 120° C. The reaction mixture was subsequently poured into benzene, mixed thoroughly and the benzene decanted from the insoluble material. The benzene solution was concentrated under vacuum to give a solid which was recrystallized from in a benzene/n-hexane mixture. The resulting product was identified to be N-(5-trifluoromethyl-1,3,4-thiadiazole) chlorodifluoroacetamide and having a melting point of 150° - 152° C.
______________________________________ N S Cl ______________________________________ C.sub.5 HC1F.sub.5 N.sub.3 OS Required, % 14.93 11.39 12.60 Found, % 15.10 11.76 12.28 ______________________________________
To a stirred suspension containing 4.2 gms of 2-amino-5-trifluoromethyl-1,3,4-thiadiazole and 2 gms of pyridine in benzene cooled at 10° C was added dropwise 4 gms of dichloroacetyl chloride. After complete addition of the dichloroacetyl chloride, the reaction mixture was refluxed for 2 hours, filtered while hot and the filtrate cooled to 5° C. The resulting solid material was separated by filtering and subsequently recrystallized from benzene to provide a product identified to be N-(5-trifluoromethyl)-1,3,4-thiadiazol-2-yl) dichloroacetamide having a melting point of 173.5° - 174.5° C.
______________________________________ C.sub.5 H.sub.2 O.sub.2 F.sub.3 N.sub.3 OS Required, % 21.45 0.72 15.01 Found, % 21.43 0.74 15.19 ______________________________________
To a stirred suspension containing 4.2 gms of 2-amino-5-trifluoromethyl-1,3,4-thiadiazol in benzene which was cooled to 10° C was added, dropwise, 4.5 gms of trichloroacetyl chloride. After complete addition of the latter, the reaction mixture was refluxed for 2 hours and subsequently concentrated under vacuum. The resulting solid residue was recrystallized from benzene to provide a product identified to be N-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)trichloroacetamide having a melting point of 121° - 122° C.
______________________________________ C H N ______________________________________ C.sub.5 HCl.sub.3 F.sub.3 N.sub.3 OS Required, % 19.06 0.32 13.34 Found, % 18.70 0.32 12.90 ______________________________________
A mixture containing 10 gms of 2-amino-5-trifluoromethyl-1,3,4-thiadiazol-and 6.7 gms of isobutyryl chloride was refluxed in benzene for 2 hours. The reaction mixture was cooled to 5° C, the solid material separated by filtering and recrystallized from aqueous methanol to provide a product identified to be N-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)isobutyramide having a melting point of 145° - 146° C.
______________________________________ C H N ______________________________________ C.sub.7 H.sub.8 F.sub.3 N.sub.3 OS Required, % 35.18 3.37 17.58 Found, % 34.68 3.30 17.78 ______________________________________
A mixture containing 5.07 gms of 2-amino-5-trifluoromethyl-1,3,4-thiadiazole and 3.45 gms of cyclopropane carboxylic chloride was stirred and refluxed for 3 hours in 100 mls of benzene. The reaction mixture was filtered and the filtrate concentrated under vacuum to a solid which was subsequently recrystallized from benzene to provide a product identified to be N-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)cyclopropane carboxamide having a melting point of 205° - 206° C.
______________________________________ C H N ______________________________________ C.sub.7 H.sub.6 F.sub.3 N.sub.3 OS Required, % 35.47 2.55 17.71 Found, % 35.36 2.47 17.46 ______________________________________
A mixture containing 2.3 gms of 2-amino-5-pentafluoroethyl-1,3,4-thiadiazole and 1.3 gms of isobutyryl chloride in benzene was refluxed for about 3 hours. The reaction mixture was concentrated under vacuum and the resulting solid recrystallized from aqueous methanol to provide a product identified to be N-(pentafluoroethyl-1,3,4-thiadiazol-2-yl)isobutyramide having a melting point of 95° - 97° C.
A mixture containing 2 gms of 2-amino-5-chlorodifluoromethyl-1,3,4-thiadiazole and 2.1 gms of trichloroacetyl chloride in 50 mls of benzene was refluxed for about 6 hours. The reaction mixture was concentrated under vacuum and the resulting solid recrystallized from aqueous methanol to provide a product identified to be N-(5-chlorodifluoromethyl-1,3,4-thiadiazol-2-yl)trichloroacetamide having a melting point of 116° - 119° C.
______________________________________ C H N ______________________________________ C.sub.5 HCl.sub.4 F.sub.2 N.sub.3 OS Required, % 17.61 0.30 12.32 Found, % 17.54 0.90 12.34 ______________________________________
A mixture containing 8 gms of 2-methylamino-5-trifluoromethyl-1,3,4-thiadiazole and 4.7 gms of trichloroacetyl chloride in benzene was refluxed for about 4 hours. The resulting solution was concentrated under vacuum to provide an oil product identified to be N-methyl-N-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)trichloroacetamide.
______________________________________ C H N ______________________________________ C.sub.6 H.sub.3 Cl.sub.3 F.sub.3 N.sub.3 OS Required, % 21.97 0.92 12.81 Found, % 22.16 1.21 12.99 ______________________________________
Other examples for the preparation of representative compounds of the invention, as produced in accordance with the above methods hereinbefore described, are presented in Table I below.
TABLE I ______________________________________ Compounds corresponding to the general structure: ##STR6## Example No. R.sub.1 R.sub.2 R.sub.3 ______________________________________ 10 CF.sub.3 H H 11 CClF.sub.2 H CH(CH.sub.3).sub.2 12 CH.sub.2 CH.sub.2 CH.sub.2 Br H CCl.sub.3 13 CHF.sub.2 H CF.sub.2 Cl ______________________________________
As stated above, the compounds of the invention have utility as herbicides. Some of them may be applied to soil for use as pre- and post-emergence herbicides. Others may be used in various states of purity ranging, for example, from purified crystals to a technical crude grade. Suitable solvents for these compounds include alcohols, aqueous alcohol and ketone solutions, including acetone, and related ketones such as methyl isobutyl ketone.
Compounds of the invention were tested for post-emergence herbicidal activity. Presented below are some nonlimiting illustrations for their use in this connection.
The test procedure involved preparation of the indicated compounds as 50% wettable powders which were extended in water to obtain final spray suspensions. The active ingredient was applied at the rates (i.e. expressed as pounds of active compound per acre) indicated in the Table. Tests were made on pigweed, setaria, Johnson Grass, morning glory, tomatoes, oats, wheat, cucumbers, red kidney beans (RKB), and cotton. Generally these plants were two weeks of age at the time of application. In the case of cotton, it was in its four to six leaf stage at the time of spray application. The red kidney beans, when sprayed, were at a point in their growth where they had a well expanded set of first true leaves.
At 10 to 12 days after the spray application the results were observed. Phytotoxicity ratings were assigned based upon a scale from 0 to 10 in which 0 indicates no injuries and the number 10 indicates that all plants were killed. Representative data are presented in Table 2. In addition to the numbers, the following symbols are used to indicate the total observation made:
Des -- Desiccation
Y -- yellowing
X -- 50% desiccation
Table 3 shows additional herbicidal activity of the compounds of the invention. The first numbers in the ratio indicate the phytotoxicity rating from 0 to 10 as previously described. The second number or letter indication is whether or not there was evidence of Necroses (Ne), Retardation of growth (R), or no effect at all (0), e.g. 9:Ne.
TABLE 2 __________________________________________________________________________ POST EMERGENCE ACTIVITY PRODUCT OF Red EXAMPLE DOSE Yellow Johnsons Morning Kidney NO. LBS/ACRE Pigweed Foxtail Grass Glory Tomato Oats Wheat Cucumber Bean Cotton __________________________________________________________________________ 2 2.5 9 10 4 10 10 6 6 10 6Y 6 Des 1.25 4 8 0 10 10 4 2 7 5 5 0.625 2 7 0 10 10 0 0 2 5 0 3 2.5 6 9 6 10 8 9 7 10 10 7 1.25 4 9 3 9 7 5 5 9 7 5 0.625 2 7 2 7 5 0 0 7 5 3 4 2.5 7 8 4 10 9Y 6 6Y 10 7 4Y 1.25 4 6 2 10 8Y 3 4 10 5 3Y 0.625 3 4 0 9 7Y 0 0 9 2 2Y 5 2 5 10 8 10 8 9 5 10 7 5Xs 1 3 7 5 10 2 4 1 10 7 3Xs 0.5 1 5 2 8 0 1 0 10 6 2 s __________________________________________________________________________
TABLE 3 __________________________________________________________________________ PHYTOTOXIC RATING PRODUCT OF Barn EXAMPLE DOSE Sugar Yellow yard Crab Buck- Morning NO. LBS/ACRE Beets Corn Oats Clover Soybean Cotton Mustard Foxtail Grass Grass wheat Glory __________________________________________________________________________ 10 2 0:0 0:0 0:0 8:Ne 1:Ne 5:Ne 7:Ne 0:0 0:0 0:0 10:Ne 2:Ne 1 0:0 0:0 0:0 4:Ne 1:Ne 3:Ne 5:Ne 0:0 0:0 0:0 10:Ne 1:Ne 0.5 0:0 0:0 0:0 0:0 1:Ne 0:0 2:Ne 0:0 0:0 0:0 10:Ne 0:Ne 11 2 9:Ne 0:0 0:0 10:Ne 5:Ne 10:Ne 3:R 3:R 1:R 0:0 10:Ne 0:0 1 8:Ne 0:0 0:0 9:Ne 3:Ne 4:Ne 8:Ne 1:R 0:0 0:0 10:Ne 0:0 0.5 7:Ne 0:0 0:0 8:Ne 1:Ne 4:Ne 8:Ne 0:0 0:0 0:0 10:Ne 0:0 __________________________________________________________________________
When utilized for herbicidal purposes, compounds of the invention may be formulated in a variety of ways and concentrations for application to the locus of desired vegetation control. It is recognized that the particular type and concentration of formulation, as well as the mode of application of the active ingredient, may govern its biological activity in a given application.
Compounds of the invention may be prepared as simple solutions of the active ingredient in an appropriate solvent in which it is completely soluble at the desired concentration. Such solvent systems include water, alcohols, acetone, aqueous alcohol and acetone and other organic solvents. These simple solutions may be further modified by the addition of various surfactants, emulsifying or dispersing agents, colorants, odorants, antifoaming agents, other herbicides or herbicidal oils which supplement or synergize the activity of the herbicides of the invention, or other adjuvants for any given application where deemed desirable to impart a particular type or degree of plant responses.
Compounds of the invention may also be formulated in various types of formulations commonly recognized by those skilled in the art of agricultural or industrial chemicals. These formulations include, for example, compositions containing the active ingredient as granules of relatively large particle size, as powder dusts, as wettable powders, as emulsifiable concentrates or as a constituent part of any other known type of formulation commonly utilized by those skilled in the art. Such formulations include the adjuvants and carriers normally employed for facilitating the dispersion of active ingredient for agricultural and industrial applications of phytotoxicants. These formulations may contain as little as 0.25% or more than 95% by weight of the active ingredient.
Dust formulations are prepared by mixing the active ingredient with finely divided solids which act as dispersants and carriers for the phytotoxicant in applying it to the locus of application for vegetation control. Typical solids which may be utilized in preparing dust formulations of the active ingredients of the invention include talc, kieselguhr, finely divided clay, fullers' earth, or other common organic or inorganic solids. Solids utilized in preparing dust formulations of the active ingredient normally have a particle size of 50 microns or less. The active ingredient of these dust formulations is present commonly from as little as 0.25% to as much as 30% or more by weight of the composition.
Granular formulations of the active ingredients are prepared by impregnating or adsorbing the toxicant on or into relatively coarse particles of inert solids such as sand, attapulgite clay, gypsum, corn cobs or other inorganic or organic solids. The active ingredient of these granular formulations is commonly present from 1.0% to as much as 20.0% or more by weight of the composition.
Wettable powder formulations are solid compositions of matter wherein the active ingredient is absorbed or adsorbed in or on a sorptive carrier such as finely divided clay, talc, gypsum, lime, wood flour, fullers' earth, kiesselguhr, or the like. These formulations preferably are made to contain 50% to 80% of active ingredient. These wettable powder formulations commonly contain a small amount of a wetting, dispersing or emulsifying agent to facilitate dispersion in water or other liquid carrier utilized to distribute the phytotoxicant to the locus of desired vegetation control.
Emulsifiable concentrate formulations are homogeneous liquid or paste compositions containing the active ingredient which will disperse in water or other liquid carrier to facilitate application of the phytotoxicant to the locus of desired vegetation control. Such emulsifiable concentrate formulations of the active ingredients may contain only the active ingredient with a liquid or solid emulsifying agent or may contain other relatively nonvolatile organic solvents such as isophorones, dioxane, heavy aromatic naphthas, xylene, or dimethyl formamide. The active ingredient in such formulations commonly comprises 10.0% to 70.0% by weight of the phytotoxicant composition.
In place of the particular compounds used in the Examples, other compounds, as hereinbefore described and taught, may also be employed to provide substantially the same results.
Claims (24)
1. A herbicidal composition comprising a carrier and a herbicidal amount of at least one compound having the general formula: ##STR7## wherein R1 is trifluoromethyl, chlorodifluoromethyl or pentafluoroethyl,
R2 is hydrogen or C1 -C4 alkyl, and
R3 is hydrogen, C1 -C4 alkyl, C1 -C4 haloalkyl or cyclopropyl, the halogen being fluorine, chlorine or bromine.
2. The composition of claim 1 wherein R1 is trifluoromethyl, R2 is hydrogen and R3 is trichloromethyl.
3. The composition of claim 1 wherein R1 is trifluoromethyl, R2 is hydrogen and R3 is chlorodifluoromethyl.
4. The composition of claim 1 wherein R1 is trifluoromethyl, R2 is hydrogen and R3 is dichloromethyl.
5. The composition of claim 1 wherein R1 is trifluoromethyl, R2 is hydrogen and R3 is isopropyl.
6. The composition of claim 1 wherein R1 is trifluoromethyl, R2 is hydrogen and R3 is cyclopropyl.
7. The composition of claim 1 wherein R1 is pentafluoroethyl, R2 is hydrogen and R3 is isopropyl.
8. The composition of claim 1 wherein R1 is chlorodifluoromethyl, R2 is hydrogen and R3 is trichloromethyl.
9. The composition of claim 1 wherein R1 is trifluoromethyl, R2 is methyl and R3 is trichloromethyl.
10. The composition of claim 1 wherein R1 is chlorodifluoromethyl, R2 is hydrogen and R3 is isopropyl.
11. The composition of claim 1 wherein R1 is trifluoromethyl, R2 is hydrogen and R3 is hydrogen.
12. A method for controlling plants which comprises applying to the locus to be treated, a herbicidal amount of at least one compound having the general formula: ##STR8## wherein, R1 is trifluoromethyl, chlorodifluoromethyl or pentafluoroethyl,
R2 is hydrogen or C1 -C4 alkyl, and
R3 is hydrogen, C1 -C4 alkyl, C1 -C4 haloalkyl or cyclopropyl, the halogen being fluorine, chlorine or bromine.
13. The method of claim 12 wherein R1 is trifluoromethyl, R2 is hydrogen and R3 is trichloromethyl.
14. The method of claim 12 wherein R1 is trifluoromethyl, R2 is hydrogen and R3 is chlorodifluoromethyl.
15. The method of claim 12 wherein R1 is trifluoromethyl, R2 is hydrogen and R3 is dichloromethyl.
16. The method of claim 12 wherein R1 is trifluoromethyl, R2 is hydrogen and R3 is isopropyl.
17. The method of claim 12 wherein R1 is trifluoromethyl, R2 is hydrogen and R3 is cyclopropyl.
18. The method of claim 12 wherein R1 is pentafluoroethyl, R2 is hydrogen and R3 is isopropyl.
19. The method of claim 12 wherein R1 is chlorodifluoromethyl, R2 is hydrogen and R3 is trichloromethyl.
20. The method of claim 12 wherein R1 is trifluoromethyl, R2 is methyl and R3 is trichloromethyl.
21. The method of claim 12 wherein R1 is chlorodifluoromethyl, R2 is hydrogen and R3 is isopropyl.
22. The method of claim 12 wherein R1 is trifluoromethyl, R2 is hydrogen and R3 is hydrogen.
23. The composition of claim 1 wherein R1 is trifluoromethyl, R2 is butyl and R3 is trichloromethyl.
24. The method of claim 12 wherein R1 is trifluoromethyl, R2 is butyl and R3 is trichloromethyl.
Priority Applications (1)
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US05/012,135 US4092148A (en) | 1970-02-17 | 1970-02-17 | Amide derivatives of 1,3,4-thiadiazoles |
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US05/012,135 US4092148A (en) | 1970-02-17 | 1970-02-17 | Amide derivatives of 1,3,4-thiadiazoles |
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US05/012,135 Expired - Lifetime US4092148A (en) | 1970-02-17 | 1970-02-17 | Amide derivatives of 1,3,4-thiadiazoles |
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Cited By (6)
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US4187098A (en) * | 1978-11-24 | 1980-02-05 | Gulf Oil Corporation | Selectively herbicidal N-(5-substituted-2-thiadiazolyl)-thiocarboxamides |
US4237302A (en) * | 1978-09-29 | 1980-12-02 | Gulf Oil Corporation | Dichloroacetylimino herbicide antagonists as plant protection agents |
US4264616A (en) * | 1980-08-29 | 1981-04-28 | Gulf Oil Corporation | 2-Iodoacetylimino-3-methyl-5-trifluoromethyl-1,3,4-thiadiazol-4-ine and use as a fungicide |
US4279636A (en) * | 1978-09-29 | 1981-07-21 | Gulf Oil Corporation | Dichloroacetylimino herbicide antagonists as plant protection agents |
US4337081A (en) * | 1979-01-23 | 1982-06-29 | Olin Corporation | 5-Amido-3-trihalomethyl-1,2,4-thiadiazoles and their use as herbicides |
US4382142A (en) * | 1978-10-18 | 1983-05-03 | Kowa Co., Ltd. | Thiadiazole derivatives and process for preparing same |
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US3429688A (en) * | 1962-05-28 | 1969-02-25 | Ciba Ltd | Method for combating undesired plant growth |
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US3573317A (en) * | 1968-08-12 | 1971-03-30 | Olin Corp | 3-trichloromethyl-5-substituted-1,2,4-thiadiazoles |
US3629275A (en) * | 1968-08-29 | 1971-12-21 | Bayer Ag | Carboxylic acid (1 2 4-thiadiazol-5-yl)-amides |
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US3429688A (en) * | 1962-05-28 | 1969-02-25 | Ciba Ltd | Method for combating undesired plant growth |
BE736854A (en) | 1968-08-01 | 1970-02-02 | ||
US3573317A (en) * | 1968-08-12 | 1971-03-30 | Olin Corp | 3-trichloromethyl-5-substituted-1,2,4-thiadiazoles |
US3629275A (en) * | 1968-08-29 | 1971-12-21 | Bayer Ag | Carboxylic acid (1 2 4-thiadiazol-5-yl)-amides |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4237302A (en) * | 1978-09-29 | 1980-12-02 | Gulf Oil Corporation | Dichloroacetylimino herbicide antagonists as plant protection agents |
US4279636A (en) * | 1978-09-29 | 1981-07-21 | Gulf Oil Corporation | Dichloroacetylimino herbicide antagonists as plant protection agents |
US4382142A (en) * | 1978-10-18 | 1983-05-03 | Kowa Co., Ltd. | Thiadiazole derivatives and process for preparing same |
US4187098A (en) * | 1978-11-24 | 1980-02-05 | Gulf Oil Corporation | Selectively herbicidal N-(5-substituted-2-thiadiazolyl)-thiocarboxamides |
US4337081A (en) * | 1979-01-23 | 1982-06-29 | Olin Corporation | 5-Amido-3-trihalomethyl-1,2,4-thiadiazoles and their use as herbicides |
US4264616A (en) * | 1980-08-29 | 1981-04-28 | Gulf Oil Corporation | 2-Iodoacetylimino-3-methyl-5-trifluoromethyl-1,3,4-thiadiazol-4-ine and use as a fungicide |
EP0047052A1 (en) * | 1980-08-29 | 1982-03-10 | Gulf Oil Corporation | 2-Iodoacetylimino-3-methyl-5-trifluoromethyl-1,3,4-thiadiazol-4-ine and use as a fungicide |
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